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WO1998002424A1 - N-(5-isothiazolyl)-thioamides substitues - Google Patents

N-(5-isothiazolyl)-thioamides substitues Download PDF

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Publication number
WO1998002424A1
WO1998002424A1 PCT/EP1997/003523 EP9703523W WO9802424A1 WO 1998002424 A1 WO1998002424 A1 WO 1998002424A1 EP 9703523 W EP9703523 W EP 9703523W WO 9802424 A1 WO9802424 A1 WO 9802424A1
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WO
WIPO (PCT)
Prior art keywords
fluorine
atoms
alkyl
chlorine
halogen atoms
Prior art date
Application number
PCT/EP1997/003523
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German (de)
English (en)
Inventor
Markus Heil
Thomas Bretschneider
Gerd Kleefeld
Christoph Erdelen
Andreas Turberg
Norbert Mencke
Original Assignee
Bayer Aktiengesellschaft
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Bayer Aktiengesellschaft filed Critical Bayer Aktiengesellschaft
Priority to JP10505570A priority Critical patent/JP2000515135A/ja
Priority to AU35410/97A priority patent/AU3541097A/en
Priority to EP97931766A priority patent/EP0912532A1/fr
Priority to BR9710322A priority patent/BR9710322A/pt
Publication of WO1998002424A1 publication Critical patent/WO1998002424A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
    • C07D275/02—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings
    • C07D275/03—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2

Definitions

  • the present invention relates to new substituted N- (5-isoth ⁇ azolyl) thioamido processes for their preparation and their use for controlling animal pests
  • N- (5-isoth ⁇ azolyl) amide insecticidal properties have properties (see, for example, WO 95/3] 448 and DE 195 42 372).
  • R 1 represents alkyl, haloalkyl, alkoxyalkyl, alkylthioalkyl, alkoxy, alkylthio or optionally substituted cycloalkyl,
  • R 2 represents hydrogen, halogen, cyano, nitro, thiocyanato, alkoxycarbonyl, alkenyloxycarbonyl, alkylthio, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl or thiocarbamoyl,
  • R represents hydrogen, alkyl, haloalkyl, alkoxyalkyl, alkylcarbonyl, alkylsulfonyl, in each case optionally substituted arylcarbonyl, arylsulfonyl or arylalkyl or optionally substituted cycloalkyl,
  • R 4 represents optionally substituted aryl, optionally substituted cycloalkyl or optionally substituted cycloalkenyl and Y represents optionally substituted alkylene, alkenyl or alkyleneoxy.
  • R 4 and Y have the meaning given above and
  • G represents a leaving group, for example halogen
  • R 4 and Y have the meaning given above and Alk represents alkyl (for example methyl or ethyl) or CH 2 COOM, where
  • M represents an alkali metal (for example sodium or potassium),
  • R 1 , R 2 , R ⁇ R 4 and Y have the meaning given above,
  • R 1 preferably represents C
  • CC 4 -alkylthio or represents optionally mono- to trisubstituted by identical or different substituents from C] -C4 alkyl or halogen CC cyclo- -alkyl
  • R 2 is preferably hydrogen, halogen, cyano, nitro, thiocyanato, C-- C 4 -alkoxy-carbonyl, C 2 -C 4 -alkenyloxy-carbonyl, C, -C -alkylthioo, - -C, -
  • Haloalkylthio with 1 to 5 identical or different halogen atoms such as fluorine and chlorine atoms, C
  • R 1 preferably represents hydrogen, C, -C 4 -alkyl, C, -C 4 -haloalkyl with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C ] -C 4 -alkoxy-C, -C 4 -alkyl, C, -C 4 alkylcarbonyl, C, -C 4 alkyl - sulfonyl, each optionally monosubstituted to trisubstituted, identically or differently, in phenylcarbonyl, phenylsulfonyl or benzyl, where in each case halogen, nitro, cyano , C, -C 4 - alkyl, C, -C 2 haloalkyl having 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C r C 4 alkoxy, C, -C 4 alkylthio, C, -C 7
  • R 4 preferably represents phenyl which is monosubstituted to trisubstituted identically or differently, the substituents being halogen, nitro, cyano, C r C ] 2 -alkyl, C, -C 12 -haloalkyl having 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C Cp-alkoxy, C - C 12 haloalkoxy with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C, -C p -alkylthio, C p -halogenal- alkylthio with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, CVC 12 alkenyl, C 2 -C p -halogenalkenyl with 1 to 5 identical or different halogen atoms, such as fluorine and chlorato, optionally one to three times, identical or differently, by C
  • C- -C 4 alkylsulfonyl C - C 4 -haloalkylsulfonyl having 1 to 5 identical Odei different halogen atoms, such as fluorine and chlorine atoms, C, -C 4 alkyl carbonyl, C - C 4 alkoxy-carbonyl, thiocarbamoyl, C] -C 4 -Alkox ⁇ m ⁇ no-C] - C, alkyl or optionally substituted by C, -C 4 alkyl-substituted Oxdiazoly! substituted phenyl, phenoxy, phenylthio, benzyl or benzyloxy in
  • C r C 6 alkylene preferably represents C r C 6 alkylene, C 1 -C 6 hydroxyalkylene, C, -C 4 alkoxy C, -C 6 -alkylene, C
  • R 1 particularly preferably represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl; CH 2 F, CHF 2 , CF ⁇ , CH 2 CI, CH 2 Br, CHCICFF ,; Methoxy, ethoxy,
  • Methoxymethyl ethoxymethyl
  • Methylthiomethyl or cyclopropyl.
  • R 2 particularly preferably represents hydrogen, chlorine, bromine, cyano, nitro, thiocyanato; Methoxycarbonyl, ethoxycarbonyl, i-propoxycarbonyl, n-propoxycarbonyl; Allyloxycarbonyl, SCF ⁇ , SCC1 2 F, SOCF- ⁇ , SOCCUF, SO F ,, S0 CCI 2 F, SCHF 2 , SOCHF 2 , S0 2 CHF 2 or CSNH 2 .
  • W particularly preferably represents hydrogen, methyl, ethyl, n- or i-propyl
  • R particularly preferably represents phenyl which is monosubstituted to trisubstituted by identical or different substituents, the substituents being halogen, nitro, cyano, C - C p -alkyl, C - C p -haloalkyl having I to 5 identical or different halogen atoms, such as Fluorine and chlorine atoms, C - C alkoxy, C r C 4 haloalkoxy with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C
  • Fluorine or chlorine atoms C, -C 4 -alkylthio-C r C 4 -alkyl, C r C 4 -alkylsulfonyl, C, -C 4 -haloalkylsulfonyl with 1 to 5 identical or different halogen atoms, such as fluorine or chlorine atoms, C , -C -alkyl-carbonyl, C r C 4 - Alkoxy-carbonyl, thiocarbamoyl, C ] -C 4 -alkoximino-C ] -C, -alkyl or optionally substituted by C, -C T alkyl l, 2,4-oxydazolyl-3-yl substituted phenoxy, phenylthio or benzyloxy in question come
  • Y is particularly preferably one of the groups
  • -CH -CH CII- or -CH 2 0-, with the left side in each case the group is linked to the thiocarbonyl group
  • R i very particularly preferably represents methyl, ethyl, n- or i-propyl, n-, i-,
  • R ⁇ very particularly preferably represents hydrogen, chlorine, bromine, cyano, nitro, thiocyanato, methoxycarbonyl or ethoxycarbonyl
  • R 1 very particularly preferably represents hydrogen, methyl, ethyl, methoxymethyl, ethoxymethyl, methylcarbonyl, phenylcarbonyl or methylsulfo-] ⁇ ⁇ nyl
  • R very particularly preferably represents phenyl which is monosubstituted to trisubstituted by identical or different substituents, the substituents being fluorine, chlorine, bromine, nitro, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, 0 methylthio, CF 3 , OCF 3 , OCHF 2 , SCF 3 , SCC1 2 F, CH 2 Br , CH 2 C1 and optionally single to triple, identical or different by fluorine, chlorine, bromine, nitro, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, Ethoxy, n- or i-
  • Y very particularly preferably represents -CH 2 - or -CH (CH 3 ) -.
  • Preferred compounds according to the invention are substances of the formulas (IA) or (IB)
  • R 1 , R 2 and R ? stand for the abovementioned general, preferred, particularly preferred and very particularly preferred meanings and
  • X 1 , X 2 , X 3 and X 4 can also each represent hydrogen
  • Another preferred group of compounds are those of the formulas (IA) or (IB), in which the phenoxy radical para to the NR'-CS-CH 7 - or
  • the compounds of the formula are very particularly preferred
  • hydrocarbon radicals such as alkyl or alkenyl - also in connection with heteroatoms such as alkoxy or alkylthio - are in each case straight-chain or branched as far as possible
  • N- (5-isothiazolyl) amides of the formula (II) required as starting materials for carrying out the processes (Aa) and (Ab) according to the invention are largely known (cf. the patent applications cited at the beginning) or can be prepared by the processes described therein
  • the compounds of the formula (III) which are furthermore to be used as starting materials in the process (Aa) according to the invention are generally known compounds of organic chemistry.
  • G preferably represents imidazolyl (cf. eg Liebigs Ann Chem 739, 201 (1970))
  • Alk preferably represents methyl or CH 2 COONa
  • the dithioesters of the formula (IV) are known (see, for example, Tetrahedron 2663 (1984), J Chem Research (M) 2701 (1988), Chem Ind (London) 803, 1974, Russ Chem Rev 45, 1035 (1976)) and / or can be produced by known, analog processes
  • Process (B) preferably phosphorus pentasulfide or Lawesson's reagent [2,4- B ⁇ s (4-methoxyphenyl) -l, 3,2,4-d ⁇ thiad ⁇ phosphetan-2,4-d ⁇ th ⁇ on] (see also Tetrahedron Vol 41, No 22, 5061 ff (1985)) in question Process (Aa) described above for the preparation of the compounds of the film (I) is carried out in the presence of a diluent. All customary solvents can be used as diluents
  • Halogenated aliphatic or aromatic hydrocarbons, ethers or nitriles such as, for example, cyclohexane, toluene , can preferably be used .
  • Bases which can be used in process (Aa) are all customary proton acceptors.
  • Alkali or alkaline earth metal hydroxides, alkali metal or alkaline earth metal carbonates or hydrogen carbonates or nitrogen bases can preferably be used. Examples include sodium hydroxide, calcium hydroxide, potassium carbonate, sodium hydrogen carbonate, triethylamine, dibenzylamine, diisopropylamine, Pv ⁇ din
  • DABCO diazabicyclooctane
  • DBN diazabicyclonones
  • DBU diazabicycloundecene
  • reaction temperatures can be varied within a wide range in the process (Aa) described. In general, temperatures between -40 ° C. and + 200 ° C., preferably between 0 ° C. and 100 ° C.
  • Suitable diluents for carrying out the process (Ab) according to the invention are all customary solvents.
  • Halogenated aliphatic or aromatic hydrocarbons such as methylene chloride, dichloroethane, cyclohexane, toluene or chlorobenzene, can preferably be used
  • reaction temperatures can be varied within a substantial range. In general, temperatures between 0 ° C. and 150 ° C., preferably between 20 ° C. and 120 ° C.
  • Preferred diluents for carrying out process (B) according to the invention are hydrocarbons, such as toluene, xylene, tetralin
  • reaction temperatures can be varied within a substantial range. In general, temperatures between 0 ° C. and 200 ° C., preferably between 20 ° C. and 150 ° C.
  • the compounds of formula (I) can also be obtained by using 5-isothiazolyl isothiocyanates of formula (VI)
  • R 1 and R 2 have the meaning given above
  • R 1 , R 2 , R and R 4 have the meaning given above,
  • R 1 , R 2 and R ⁇ have the meaning given above,
  • E represents hydrogen or methyl
  • R 4 has the meaning given above
  • substituted N- (5-isoth ⁇ azolyl) thioamides of the formula (I) according to the invention can, if appropriate, be converted into their corresponding N-oxide or salt derivatives in a known manner and these are also the subject of the present application
  • the active substances are suitable for combating animal pests, in particular insects, arachnids and nematodes, which occur in agriculture, in forests, in the protection of stocks and materials and in the hygiene sector. They can preferably be used as crop protection products effective against normally sensitive and resistant species as well as against all or individual stages of development
  • the pests mentioned above include From the order of the Isopoda, for example Oniscus asellus, Armadillidium vulgare, Porcellio scaber
  • Thysanoptera for example Hercinothrips femoralis, Th ⁇ ps tabaci
  • Heteroptera e.g. Eurygaster spp, Dysdercus intermedius, Piesma quadrata, Cimex lectula ⁇ us, Rhodnius prolixus, T ⁇ atoma spp
  • From the order of the Homoptera for example Aleurodes brassicae, Bemisia tabaci, T ⁇ aleurodes vaporanorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ⁇ bis, Aphis fabae, Aphis pomi, E ⁇ osoma lanigerum, Hyalopterus arundinis, Phylloxemaxphiphosum, Phppoxera macrophorus, sppaoxemphiphidumx humuh, Rhopalosiphum padi, Empoasca spp, Euscehs bilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax stnatellus, Nilaparvata lugens, Aonidiella aurantn, Aspidiotus hederae, Pseudococcus spp, P
  • Bucculat ⁇ x thurbenella Phyllocnistis citrella, Agrotis spp, Euxoa spp, Feltia spp, Ea ⁇ as insulana, Heliothis spp, Spodoptera exigua, Mamestra brassicae, Panohs flammea, Spodoptera litura, Spodoptera spp, T ⁇ choplusiao sil, T ⁇ choplusiao npp , Ephestia kuehniella, Galle ⁇ a mellonella, Tineola bisselliella, Tinea pelhonella, Hofmannophila pseudospretella,
  • Cacoecia podana Capua reticulana, Cho ⁇ stoneura fumiferana, Clysia ambiguella 1 lomona magnanima, l ortri ⁇ vi ⁇ dana
  • Hymenoptera From the order of Hymenoptera, for example Dip ⁇ on spp, Hoplocampa spp, Lasius spp, Monomo ⁇ um pharaonis, Vespa spp
  • Drosophila melanogaster Musca spp, Fannia spp, Calhphora erythrocephala, Lucilia spp, Chrysomyia spp, Cuterebra spp, Gastrophilus spp, Hyppobosca spp, Stomoxys spp, Oestrus spp, Hypoderma spp, Tabanus spp, Tanniaulppia sppanppella hppiappella, Bibio , Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae, Tipula paludosa
  • Siphonaptera for example Xenopsylla cheopis
  • Ceratophyllus spp From the order of the Arachnida for example Scorpio maurus, Latrodectus mactans.
  • Acarina for example Acarus siro, Argas sp, Ornithodoros spp, Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp, Rhipicephalus spp., Amblyomma spp, Hyalomma spp, Ixodes spp, Psoroptes spp, Choricoptes spp, Choricoptes spp, Chori Tarsonemus spp, Bryobia praetiosa,
  • Plant parasitic nematodes include, for example, Pratylenchus spp, Radopholus similis, Ditylenchus dipsaci, Tylenchulus semipenetrans, Heterodera sp, Globodera spp, Meloidogyne spp, Aphelenchoides spp, Longidorus spp, Xiphinema spp, Trichodor spp
  • the compounds of the formula (I) according to the invention are notable in particular for high insecticides and acaricidal activity
  • Rice cicada (Nephotettix cinct ⁇ ceps) and the caterpillars of the owl butterfly (Spodoptera frugiperda) or for combating plant-damaging mites, such as against the common spider mite (Tetranychus urticae)
  • the active ingredients can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusting agents, pastes, soluble powders, granules, suspension emulsion concentrates, active ingredient-impregnated natural and synthetic substances and very fine encapsulations in polymers Fabrics
  • formulations are prepared in a known manner, for example by mixing the active ingredients with extenders, that is to say liquid solvents and / or solid carriers, if appropriate using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents
  • organic solvents can, for example, also be used as auxiliary solvents come essentially into question aromatics, such as xylene, toluene, or alkyl naphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example petroleum fractions, mineral and vegetable oils, alcohols , such as butanol or glycol and their ethers and esters,
  • Ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethyl form am id and dimethyl sulfoxide, and water
  • Possible solid carriers are, for example, ammonium salts and natural rock powders such as kaolins, clays,
  • Talc such as highly disperse silica, aluminum oxide and silicates, as solid carrier materials for granules are, for example, broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic Granules from inorganic and organic flours as well
  • Granules of organic material such as sawdust, coconut shells, corn cobs and tobacco stalks, emulsifiers and / or foam-producing agents are suitable, for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, Alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates, as dispersants are, for example, lignin sulfite waste liquors and methyl cellulose
  • Adhesives such as carboxymethyl cellulose, natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids such as cephalins and lecithins and synthetic phospholipids can be used in the formulations
  • additives can be mineral and vegetable oils
  • Dyes such as inorganic pigments, for example iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used
  • the formulations in general contain between 0.1 and 95% by weight of active compound, preferably between 0.5 and 90%
  • active compound according to the invention can be present in its commercially available formulations and in the use forms prepared from these formulations in a mixture with other active compounds, such as insecticides, attractants, stenlants, bactericides, acanzides, nematicides, fungicides, growth-regulating substances or herbicides.
  • active compounds include, for example, phosphorus acid esters, carbamates, carboxylic acid esters, chlorinated hydrocarbons, phenylureas, substances produced by microorganisms and others
  • Fungicides 2-aminobutane, 2-anion-4-methyl-6-cyclopropyl-py ⁇ m ⁇ d ⁇ n, 2 ', 6'-d ⁇ b ⁇ omo-2-methyl-4'-t ⁇ fluoromethoxy-4'-t ⁇ ⁇ fluoro-methyl-l, 3-th ⁇ azoi-5-ca ⁇ boxan ⁇ l ⁇ d, 2,6-D ⁇ - chloro-N- (4-t ⁇ fluoromethylbenzyl) -benzam ⁇ d, (E) -2-methoxy ⁇ m ⁇ no-N-methyl-2- (2-phenoxyphenyl) -acetam ⁇ d, 8th -Hydroxyqu ⁇ nol ⁇ nsulfat, methyl- (E) -2- ⁇ 2- [6- (2-cyano-pheno ⁇ y) -py ⁇ m ⁇ d ⁇ n-4-yloxy] -phenyl ⁇ -3-methoxyacrylate, M ethyl - (E) -methox ⁇
  • Mancopper Mancozeb, Maneb, Mepanipy ⁇ m
  • Mepronil Metalaxyl
  • Metconazol Methasulfocarb, Methfuroxain, Metiram, Metsulfovax, Myclobutanil,
  • Tebuconazole Tecloftalam, Tecnazen, Tetraconazole, Thiabendazole, Thicyofen, Thiophanat-methyl, Thiram, Tolclophos-methyl, Tolylfluamd, T ⁇ adimefon, T ⁇ adimenol, T ⁇ azoxid, T ⁇ chlamid, T ⁇ cyclazol, T ⁇ demorphol, T ⁇ demorphol, T ⁇
  • Fenamiphos Fenazaquin, Fenbutatinoxid, Fenitrothion, Fenobucarb Fenothiocarb, Fenoxycarb, Fenpropath ⁇ n, Fenpyrad, Fenpyroximat, Fenthion, Fenvalerate, Fipronil, Fluazinam, Flucycloxuron, Flucythrinat, Flufenoxuron, Flufenproxophon, Fufonproxophon, Fufonproxophon, Fufonproxophon, Fufonproxophon, Fufonproxophon, Fufonproxophon, Fufonfox, Fufion, Fufion, Fufone
  • Iprobefos Iprobefos, Isazophos, Isofenphos, Isoprocarb, Isoxathion, Ivermectin, Lambda-cyhaloth ⁇ n, Lufenuron, Malathion, Mecarbam, Mervinphos, Mesulfenphos, Metaldehyde, Methac ⁇ fos, Methamidophos, Methidathion, Methiocarb, Methomyl, Metolcarb, Milbemectin, Monocrotophos, Moxidectin,
  • Parathion A Parathion M, Permeth ⁇ n, Phenthoat, Phorat, Phosalon Phosmet, Phosphamidon, Phoxim Pi ⁇ micarb, Pi ⁇ miphos M, Pi ⁇ miphos A Profenofos, Promecarb, Propaphos, Propoxur, Prothiofos, Prothoat, Pymetrozin, Pvadachaphenphion, Pyrvithachidophion, Pvrachaphthiophion, Pvrachaphrinophion, Pvrachaphrinophion, Pvrachaphthiophion, Py ⁇ proxifene
  • Tebufenozid Tebufenpyrad, Tebupi ⁇ mphos, Teflubenzuron, Tefluth ⁇ n, Temephos, Terbam, Terbufos, Tetrachlorvinphos, Thiafenox, Thiodicarb, Thiofanox, Thio-methon, Thionazin, Thu ⁇ ngiensin, Talomethathonon, Talomethathonon, Talomethathonon, Talomethathonon
  • the active compounds according to the invention can also be present in their commercially available formulations and in the use forms prepared from these formulations in a mixture with synergists.
  • Synergists are compounds by which the action of the active compounds is increased without the added synergist itself having to be active
  • the active substance content of the use forms prepared from the commercially available formulations can vary within wide ranges.
  • the application forms can be from 0.0000001 to 95% by weight of active ingredient, preferably between 0.0001 and 1% by weight
  • the application takes place in a customary manner adapted to the application forms
  • the active compounds according to the invention act not only against plant, hygienic and void pests, but also in the veterinary sector against animal parasites (ectoparasites) such as tick ticks, leather ticks and rough mites
  • Nematoce ⁇ na and Brachyce ⁇ na e.g. Aedes spp, Anopheles spp, Culex spp, Simulium spp,
  • Siphonapt ⁇ da for example Pulex spp, Ctenocephalides spp, Xenopsylla spp, Ceratophyllus spp
  • Heteropte ⁇ da for example Cimex spp, T ⁇ atoma spp, Rhodnius spp, Panstrongylus spp
  • the active compounds of the formula (I) according to the invention are also suitable for combating arthropods which are farm animals, such as, for example, cattle, sheep, goats, horses, pigs, donkeys, camels, buffalo, rabbits, chickens, turkeys, ducks, geese, bees , other domestic animals such as dogs, cats, house birds, aquarium fish and so-called experimental animals such as hamsters, guinea pigs, rats and mice.
  • arthropods are farm animals, such as, for example, cattle, sheep, goats, horses, pigs, donkeys, camels, buffalo, rabbits, chickens, turkeys, ducks, geese, bees , other domestic animals such as dogs, cats, house birds, aquarium fish and so-called experimental animals such as hamsters, guinea pigs, rats and mice.
  • the active compounds according to the invention are used in the veterinary sector in a known manner by enteral administration in the form of, for example, tablets, capsules, drinks, drenches, granules, pastes, boluses, the feed-through method, suppositories, by parenteral administration, for example by Injections (intramuscular, subcutaneous, intravenous, intraperitonal, etc.), implants, by nasal application, by dermal application in the form of, for example, diving or bathing (dipping), spraying (spray), pouring on (pour-on and Spot - on), washing, powdering and with the help of shaped bodies containing active ingredients, such as collars, ear tags, tail tags, limb tapes, holsters, marking devices, etc
  • the active compounds of the formula (I) can be used as formulations (for example powders, emulsions, flowables)
  • Agents which contain the active substances in an amount of 1 to 80% by weight, directly or after 100 to 10,000-fold dilution or use them as a chemical bath
  • insects may be mentioned by way of example and preferably, but without limitation
  • Kalotermes flavicollis Cryptotermes brevis, Heterotermes indicola, Reticulitermes flavipes, Reticulitermes santonensis, Reticulitermes lucifugus, Mastotermes darwiniensis, Zootermopsis nevadensis, Coptotermes formosanus
  • Bristle tail like Lepisma saccha ⁇ na Bristle tail like Lepisma saccha ⁇ na
  • technical materials are understood to mean non-living materials, such as preferably plastics, adhesives, glues, papers and cartons, leather, wood and wood processing products and paints
  • the material to be protected against insect infestation is very particularly preferably wood and wood processing products
  • Wood and wood processing products which can be protected by the agent according to the invention or mixtures containing it, are to be understood as examples. Lumber, wooden beams, railway sleepers, bridge parts, jetties, wooden vehicles, boxes, pallets, containers, telephone poles, wooden cladding, wooden windows and doors, plywood, chipboard, carpentry or Ilolz products, which are generally used in house construction or joinery
  • the active compounds can be used as such, in the form of concentrates or formulations which are generally customary, such as powders, granules, solutions, suspensions, ulcers or pastes
  • the formulations mentioned can be prepared in a manner known per se, for example by mixing the active compounds with at least one solvent or diluent, emulsifier, dispersant and / or binder or fixative, water repellant, optionally siccatives and UV stabilizers and, if appropriate Dyes and pigments as well as other processing aids
  • the insecticidal compositions or concentrates used to protect wood and wood-based materials contain the active compound according to the invention in a concentration of 0.0001 to 95% by weight, in particular 0.001 to 60% by weight.
  • the amount of the agents or concentrates used depends on the type and the occurrence of the insects and on the medium. The optimum amount of use can be determined in each case by use of test series. In general, however, it is sufficient 0.0001 to 20% by weight. , preferably 0.001 to 10% by weight of the active ingredient, based on the material to be protected
  • An organic-chemical solvent or solvent mixture and / or an oily or oil-like heavy substance serves as the solvent and / or diluent volatile organic-chemical solvent or solvent mixture and / or a polar organic-chemical solvent or solvent mixture and / or water and optionally an emulsifier and / or wetting agent
  • the organic-chemical solvents used are preferably oily or oil-like solvents with an evaporation number above 35 and a flash point above 30 ° C., preferably above 45 ° C.
  • Suitable mineral oils or their aromatic fractions or mineral oil-containing solvent mixtures are difficultly volatile, water-insoluble, oily and oil-like solvents.
  • Mineral oils with a boiling range of 170 to 220 ° C, white spirit with a boiling range of 170 to 220 ° C, spindle oil with a boiling range of 250 to 350 ° C, petroleum or aromatics with a boiling range of 160 to 280 ° C, turpentine oil are advantageous and the like for use
  • organic semi-volatile oily or oil-like solvents with an evaporation number above 35 and a flash point above 30 ° C, preferably above 45 ° C can be partially replaced by slightly or medium-volatile organic chemical solvents, with the proviso that the solvent mixture also has an evaporation number 35 and a flash point above 30 ° C, preferably above 45 ° C, and that the insecticide-fungicide mixture is soluble or emulsifiable in this solvent mixture
  • part of the organic-chemical solvent or solvent mixture is replaced by an aphatic polar organic-chemical solvent or solvent mixture.
  • Aliphatic organic-chemical solvents such as glycol ethers containing hydroxyl and / or ester and / or ether groups are preferably used , Ester or the like for use
  • the known organic-chemical binders are synthetic resins which are known to be water-thinnable and / or soluble or dispersible or emulsifiable in the organic-chemical solvents used and / or binding drying oils, in particular binders consisting of or containing an acrylate resin , a vinyl resin, e.g. polyvinyl acetate,
  • Polyester resin polycondensation or polyaddition resin, polyurethane resin, alkyd resin or modified alkyd resin, phenolic resin, hydrocarbon resin such as indene-coumarone resin, silicone resin, drying vegetable and / or drying oils and / or physically drying binders based on a natural rubber and / or synthetic resin
  • the synthetic resin used as a binder can be used in the form of an emulsion, dispersion or solution. Bitumen or bituminous substances up to 10% by weight can also be used as binders. In addition, known dyes, pigments, water-repellent agents, odorants and Inhibitors or corrosion protection agents and the like are used
  • At least one alkyd resin or modified alkyd resin and / or a drying vegetable oil is preferably contained in the agent or in the concentrate as organic-chemical binder.
  • binder mentioned can be replaced by a fixative (gem ⁇ sch) or a plasticizer (gem ⁇ sch). These additives are intended to prevent volatilization of the active ingredients and crystallization or precipitation, preferably they replace 0.01 to 30% of the binder (based on to 100% of the binder used)
  • the plasticizers originate from the chemical classes of phthalic acid esters such as dibutyl, dioctyl or benzyl butyl phthalate, phosphoric acid esters such as t ⁇ butyl phosphate, adipic acid esters such as di (2-ethylhexyl) adipate, stearates such as butyl stearate or amyl stearate, oleates such as butyl ether and olefinic glyceryl ether - Kolether, Glyce ⁇ nester and p-Toluenesulfonsaureestcr
  • Fixing agents are chemically based on polyvinyl alkyl ethers such as polyvinyl methyl ether or ketones such as benzophenone and ethylene benzophenone Water is also particularly suitable as a solvent or diluent, optionally in a mixture with one or more of the above-mentioned organic chemical solvents or diluents, emulsifiers and dispersants
  • a particularly effective wood protection is achieved by large-scale impregnation processes, eg vacuum, double vacuum or printing processes
  • the ready-to-use compositions can optionally contain further insecticides and, if appropriate, one or more fungicides
  • Possible additional admixtures are preferably the insecticides and lungicides mentioned in WO 94/29 268. Those mentioned in this document
  • Insecticides such as chloropyphosph, phoxime, silafluofin, ⁇ lphameth ⁇ n, cyfluth ⁇ n, cypermeth ⁇ n, delta-meth ⁇ n, permeth ⁇ n, imidaclop ⁇ d, NI-25, flufenoxuron, hexaflumuron and toxy-fungazazole, epoxy-fazazole, and epoxungazonole, as well as epifungazonole, as well as epoxungazon, as well as epoxungazon, as well as epifungazon, as Azaconazole, Propiconazole, Tebuconazole, Cyproconazole, Mctconazole, Imazalil, Dichlorfluanid, Tolylfluanid, 3-Iodo-2-propionyl-butylcarbamate N-octyl- ⁇ soth ⁇ azol ⁇ n-3-o ⁇ and 4,5-
  • active compound 1 part by weight of active compound is mixed with the stated amount of solvent and the stated amount of emulsifier, and the concentrate is diluted with water egg to the desired concentration
  • Cabbage leaves (Brassica oleracea) are 'I themselves in the preparation of active dei desired concentration treated and staffed with Meerrettichblattkafer larvae Phaedon cochlea ⁇ ae as long as the leaves are still moist
  • the death rate is determined in%. 100% means that all the beetle larvae have been killed, 0% means that no beetle larvae have been killed

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

La présente invention concerne de nouveaux N-(5-isothiazolyl)-thioamides de la formule (I) dans laquelle R?1, R2, R3, R4¿, et Y ont la notation donnée dans la description, des procédés pour les préparer et leur utilisation pour lutter contre les parasites animaux.
PCT/EP1997/003523 1996-07-16 1997-07-03 N-(5-isothiazolyl)-thioamides substitues WO1998002424A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
JP10505570A JP2000515135A (ja) 1996-07-16 1997-07-03 置換されたｎ―（５―イソチアゾリル）チオアミド類
AU35410/97A AU3541097A (en) 1996-07-16 1997-07-03 Substituted n-(5-isothiazolyl) thioamides
EP97931766A EP0912532A1 (fr) 1996-07-16 1997-07-03 N-(5-isothiazolyl)-thioamides substitues
BR9710322A BR9710322A (pt) 1996-07-16 1997-07-03 Tioamidas N-(5-isotiazolil) substituidas

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE1996128569 DE19628569A1 (de) 1996-07-16 1996-07-16 Substituierte N-(5-Isothiazolyl)-thioamide
DE19628569.0 1996-07-16

Publications (1)

Publication Number Publication Date
WO1998002424A1 true WO1998002424A1 (fr) 1998-01-22

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PCT/EP1997/003523 WO1998002424A1 (fr) 1996-07-16 1997-07-03 N-(5-isothiazolyl)-thioamides substitues

Country Status (7)

Country Link
EP (1) EP0912532A1 (fr)
JP (1) JP2000515135A (fr)
CN (1) CN1225632A (fr)
AU (1) AU3541097A (fr)
BR (1) BR9710322A (fr)
DE (1) DE19628569A1 (fr)
WO (1) WO1998002424A1 (fr)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000006566A1 (fr) * 1998-07-30 2000-02-10 Syngenta Limited Derives de benzoxazole, benzthiazole et benzimidazole
WO2000020415A1 (fr) * 1998-10-06 2000-04-13 Bayer Aktiengesellschaft Heterocyclylamides d'acide phenylacetique ayant un effet insecticide
WO2001055139A1 (fr) * 2000-01-28 2001-08-02 Syngenta Limited Derive d'isothiazole et utilisations de ceux-ci sous forme de pesticides
WO2001055144A1 (fr) * 2000-01-28 2001-08-02 Syngenta Limited Derives d'isothiazole et leur utilisation en tant que pesticides
WO2001055135A1 (fr) * 2000-01-28 2001-08-02 Syngenta Limited Derives d'azine utilises comme pesticides
WO2001055141A1 (fr) * 2000-01-28 2001-08-02 Syngenta Limited Derives d'azine comme pesticides
WO2001055145A1 (fr) * 2000-01-28 2001-08-02 Syngenta Limited Derives d'azine en tant que pesticides
WO2001055142A1 (fr) * 2000-01-28 2001-08-02 Syngenta Limited Derives d'isothiazole et leur utilisation comme pesticides
US7858643B2 (en) 2004-08-26 2010-12-28 Agouron Pharmaceuticals, Inc. Enantiomerically pure aminoheteroaryl compounds as protein kinase inhibitors

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005040162A1 (fr) * 2003-10-27 2005-05-06 Basf Aktiengesellschaft Composes i 5-(2-arylacetamido)isothiazole

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US3541108A (en) * 1966-04-06 1970-11-17 Merck Ag E Isothiazole derivatives
DE1954179A1 (de) * 1969-10-28 1971-05-06 Merck Anlagen Gmbh Acylaminoisothiazolsalze
WO1995031448A1 (fr) * 1994-05-17 1995-11-23 Dowelanco Pesticides de n-(5-isothiazolyle)amide
JPH08245561A (ja) * 1995-03-09 1996-09-24 Takeda Chem Ind Ltd 殺有害生物活性チオアミド誘導体、イソチアゾール誘導体、それらの用途
DE19542372A1 (de) * 1995-11-14 1997-05-15 Bayer Ag Acylierte 5-Aminoisothiazole

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US3541108A (en) * 1966-04-06 1970-11-17 Merck Ag E Isothiazole derivatives
DE1954179A1 (de) * 1969-10-28 1971-05-06 Merck Anlagen Gmbh Acylaminoisothiazolsalze
WO1995031448A1 (fr) * 1994-05-17 1995-11-23 Dowelanco Pesticides de n-(5-isothiazolyle)amide
JPH08245561A (ja) * 1995-03-09 1996-09-24 Takeda Chem Ind Ltd 殺有害生物活性チオアミド誘導体、イソチアゾール誘導体、それらの用途
DE19542372A1 (de) * 1995-11-14 1997-05-15 Bayer Ag Acylierte 5-Aminoisothiazole

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Title
DATABASE WPI Week 9648, Derwent World Patents Index; AN 96-482197, XP002044727 *
J. G. SAMARITONI ET AL.: "N-Alkyl-N-(5-isothiazolyl)- and N-(alkylisothiazolin-5-ylidene)phenylacetamides. Synthesis and biological activity", J. AGRIC. FOOD CHEM., vol. 45, no. 5, 1997, pages 1920 - 1930, XP002044726 *

Cited By (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000006566A1 (fr) * 1998-07-30 2000-02-10 Syngenta Limited Derives de benzoxazole, benzthiazole et benzimidazole
AP969A (en) * 1998-07-30 2001-05-29 Zeneca Ltd Benzazoles: benxoxazole, benzthiazole and benzimidazole derivatives.
US6544989B2 (en) 1998-07-30 2003-04-08 Syngenta Limited Benzazoles: benzoxazole, benzthiazole and benzimidazole derivatives
WO2000020415A1 (fr) * 1998-10-06 2000-04-13 Bayer Aktiengesellschaft Heterocyclylamides d'acide phenylacetique ayant un effet insecticide
US6403622B1 (en) 1998-10-06 2002-06-11 Bayer Aktiengesellschaft Phenylacetic acid heterocyclyl amides having an insecticidal effect
WO2001055137A1 (fr) * 2000-01-28 2001-08-02 Syngenta Limited Derives d'azine et leur utilisation comme pesticides
WO2001055141A1 (fr) * 2000-01-28 2001-08-02 Syngenta Limited Derives d'azine comme pesticides
WO2001055145A1 (fr) * 2000-01-28 2001-08-02 Syngenta Limited Derives d'azine en tant que pesticides
WO2001055135A1 (fr) * 2000-01-28 2001-08-02 Syngenta Limited Derives d'azine utilises comme pesticides
WO2001055142A1 (fr) * 2000-01-28 2001-08-02 Syngenta Limited Derives d'isothiazole et leur utilisation comme pesticides
WO2001055144A1 (fr) * 2000-01-28 2001-08-02 Syngenta Limited Derives d'isothiazole et leur utilisation en tant que pesticides
WO2001055139A1 (fr) * 2000-01-28 2001-08-02 Syngenta Limited Derive d'isothiazole et utilisations de ceux-ci sous forme de pesticides
JP2003523355A (ja) * 2000-01-28 2003-08-05 シンジェンタ リミテッド イソチアゾール誘導体及び有害生物殺滅剤としてそれらの使用
US6703347B2 (en) 2000-01-28 2004-03-09 Syngenta Limited Isothiazole derivatives and their use as pesticides
EP1686128A2 (fr) 2000-01-28 2006-08-02 Syngenta Limited Dérivés de l'isothiazole et leur utilisation comme pesticides
EP1686128A3 (fr) * 2000-01-28 2007-01-24 Syngenta Limited Dérivés de l'isothiazole et leur utilisation comme pesticides
US7858643B2 (en) 2004-08-26 2010-12-28 Agouron Pharmaceuticals, Inc. Enantiomerically pure aminoheteroaryl compounds as protein kinase inhibitors

Also Published As

Publication number Publication date
EP0912532A1 (fr) 1999-05-06
AU3541097A (en) 1998-02-09
CN1225632A (zh) 1999-08-11
BR9710322A (pt) 1999-08-17
JP2000515135A (ja) 2000-11-14
DE19628569A1 (de) 1998-01-22

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